Orange-red to violet dye.



UNITED STATES PATENT OFFICE.

MAX WEILER, OF ELBERFELD, GERMANY, ASSIGNOR T0 FARBENFABRIKEN VORM.

FRIEDR. BAYER & (10., OF ELBERFELD, GERMANY, A CORPORATION OF GERMANY.

No Drawing.

To all whom it may concern:

Be it known that I, MAX WEILER, doctor of philosophy, chemist, citizen of the German Empire, residing at Elberfeld, Germany, have invented new and useful Improvements in New Dyes, of which the following is a specification.

My invention relates to the manufacture and roduction of new dyestuffs which are obtained by condensin oxyaldehydes especially oxybenzaldehy es, aldehydooxybenzoic acids and their substitution products with oxycarbox lic acids and oxidizing the leuco compoun s thus obtained. The new dyestufi's can be treated on the fiber with bichromate of potassium, solid shades being thus obtained.

In order to illustrate the new process more fully the followingexample is given, the parts being by weight: A mixture of 14 parts of 4-oxy-1-benzaldehyde, 33 parts of ortho-cresotinic acid, 300 parts of sulfuric acid (60 B.) and 50 parts of glacial acetic acid are heated for 20 hours to 70 C. while stirrin until the Whole cresotinic acid has entere into reaction. The mass of the re action is poured into ice water and the leuco compound is filtered ofi. Small quantities of ortho-cresot-inic acid can be, removed by means of organic solvents. To produce the coloring matter from this leuco compound the dried product is dissolved in 5 times its quantity of concentrated sulfuric acid and this solution is stirred at 4060 C. with NaN0,. When the oxidation is finished the melt ,is oured on ice and the dye is filtered oil. It yes wool orange-red,which on aftertreatment with chrome turns red.

The new dyes are dark powders soluble in dilute caustic soda lye generally with a red color, dyeing wool from acid baths generally from orange red to violet shades, which can be chromed on the fiber.

Specification of Letters Patent.

Application filed October 26, 1909.

Serial No. 524,679.

Instead of ortho-cresotinic acid, meta-cresotinic acid, salicylic acid, par'a-oxy-benzoic acid, 2.4-dioxy-benzoic acid, chloro-salieylic acid, oxy-naphthoic acids, may be used, instead of et-oxy-l-benzaldehyde, 3- or 5- Ihethyl-Q-oxybenzaldehyde, salicylaldehyde, 2-oxy-3- or 5-chloro-benzaldeh de, Q-oXy- 3.5-dichloro-benzalElehyde, 3-c1loro-4-oxybenzaldehyde, 3.5-dichloro-4-oxy-benmidle hyde, 3-meth l-4-oxybenzaldehyde, 2-chloro- 4-oXy-benzal ehyde, 4-oxybenzaldehyde' 2- or 3-sulfonic acid, aldehydo-orthocresotinic acid, aldehydo-para-cresotinic or oxybenzoic acid, 1-aldehydo-2-oxy-4-benzoic acid, aldehydo-para-chloro-salicylic acid, 1- aldehydO-Q-oxy-5-sulfo-3-benzoic acid, 5- sulfo-2-oxybenzaldehyde, 3-sulfo-5-methyl- 2 oxybenzaldehyde, 4-diethylamino-2-oxybenzaldehyde, 3-nitro-2-oxybenzaldehyde, 5- nitro-2-oxybenzaldehyde, 2.4-dioxybenzalde- Patented Feb. 22, 1910. I

hyde, 8.4-dioxybenzaldehyde, etc. The condensation can also be carried out in another manner 6. g. with a mixture of acetic acid and sulfuric acid, a methyl alcoholic sulfuric acid, etc. The oxidation can be carried out with nitric acid, nitro compounds, etc.

I claim The herein described dyestufi's obtainable from the herein defined oxyaldehydes and .oxycarbox lic acids, which dyestuffs are dark pow ers soluble in dilute caustic soda lye generally with a red color, dyeing wool from acid baths enerally from orange red to violet shades w ich can be chromed after dyeing, substantially as described.

In testimony whereof I have hereunto set my hand in the presence of two subscribing 

